Supramolecular PEG-co-Oligo(p-benzamide)s Prepared on a Peptide Synthesizer
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- 作者：Hannah M. Kö ; nig ; Tatiana Gorelik ; Ute Kolb ; Andreas F. M. Kilbinger
- 刊名：Journal of the American Chemical Society
- 出版年：2007
- 出版时间：January 24, 2007
- 年：2007
- 卷：129
- 期：3
- 页码：704 - 708
- 全文大小：356K
- 年卷期：v.129,no.3(January 24, 2007)
- ISSN：1520-5126
文摘
An automated synthesis protocol has been developed for the preparation of oligo(p-benzamide)son solid support using a commercial peptide synthesizer employing a variation of standard Fmoc chemistry.Bis(trichloromethyl carbonate) in NMP was used to activate the aromatic carboxylic acids for acylation ofsecondary aromatic amines on solid support. N-Protected hepta(p-benzamide) was automatically preparedon solid support and manually converted to a solid supported block co-oligomer by attaching a poly(ethyleneglycol) chain. Cleavage from the support could be achieved with minimal loss of the p-methoxybenzylN-protective group. While the N-protected block co-oligomer was molecularly dissolved in nonpolar organicsolvents, the N-deprotected block co-oligomer adopted a rod-coil conformation and showed strongaggregation as evidenced by gel permeation chromatography and transmission electron microscopy. Rigidrodlike aggregates could be observed in chloroform, toluene, as well as water.